1152719-81-7Relevant articles and documents
Photocatalytic C?H Azolation of Arenes Using Heterogeneous Carbon Nitride in Batch and Flow
Wen, Zhenghui,Wan, Ting,Vijeta, Arjun,Casadevall, Carla,Buglioni, Laura,Reisner, Erwin,No?l, Timothy
, p. 5265 - 5270 (2021/10/25)
The functionalization of aryl C(sp2)?H bonds is a useful strategy for the late-stage modification of biologically active molecules, especially for the regioselective introduction of azole heterocycles to prepare medicinally-relevant compounds. Herein, we describe a practical photocatalytic transformation using a mesoporous carbon nitride (mpg-CNx) photocatalyst, which enables the efficient azolation of various arenes through direct oxidation. The method exhibits a broad substrate scope and is amenable to the late-stage functionalization of several pharmaceuticals. Due to the heterogeneous nature and high photocatalytic stability of mpg-CNx, the catalyst can be easily recovered and reused leading to greener and more sustainable routes, using either batch or flow processing, to prepare these important compounds of interest in pharmaceutical and agrochemical research.
Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication
Huang, He,Strater, Zack M.,Rauch, Michael,Shee, James,Sisto, Thomas J.,Nuckolls, Colin,Lambert, Tristan H.
supporting information, p. 13318 - 13322 (2019/08/12)
Visible-light photocatalysis and electrocatalysis are two powerful strategies for the promotion of chemical reactions. Here, these two modalities are combined in an electrophotocatalytic oxidation platform. This chemistry employs a trisaminocyclopropenium (TAC) ion catalyst, which is electrochemically oxidized to form a cyclopropenium radical dication intermediate. The radical dication undergoes photoexcitation with visible light to produce an excited-state species with oxidizing power (3.33 V vs. SCE) sufficient to oxidize benzene and halogenated benzenes via single-electron transfer (SET), resulting in C?H/N?H coupling with azoles. A rationale for the strongly oxidizing behavior of the photoexcited species is provided, while the stability of the catalyst is rationalized by a particular conformation of the cis-2,6-dimethylpiperidine moieties.
